| 1 | Wed 5 Aug | 103-0 v Immingham TownWinterton Rangers 3-0 Immingham Town | Northern Counties East League Division One |
| 2 | Sat 8 Aug | 104-3 v Harrogate Railway AthleticHarrogate Railway Athletic 3-4 Winterton Rangers | Northern Counties East League Division One |
| 3 | Wed 12 Aug | 101-2 v Harrogate Railway AthleticWinterton Rangers 1-2 Harrogate Railway Athletic | Northern Counties East League Cup First Round |
| 4 | Sat 15 Aug | 101-2 v AFC DarwenWinterton Rangers 1-2 AFC Darwen | FA Vase First Qualifying Round |
| 5 | Wed 19 Aug | 7 1-5 v Club Thorne CollieryWinterton Rangers 1-5 Club Thorne Colliery | Northern Counties East League Division One |
| 6 | Sat 5 Sep | 162-1 v Leeds UFCAWinterton Rangers 2-1 Leeds UFCA | Northern Counties East League Division One |
| 7 | Sat 12 Sep | 83-1 v Armthorpe WelfareWinterton Rangers 3-1 Armthorpe Welfare | Northern Counties East League Division One |
| 8 | Tue 15 Sep | 70-3 v Goole AFCGoole AFC 3-0 Winterton Rangers | Northern Counties East League Division One |
| 9 | Sat 19 Sep | 172-2 v Ilkley TownWinterton Rangers 2-2 Ilkley Town | Northern Counties East League Division One |
| 10 | Sat 26 Sep | 142-4 v Brigg TownBrigg Town 4-2 Winterton Rangers | Northern Counties East League Division One |
| 11 | Wed 30 Sep | 162-0 v Kinsley BoysWinterton Rangers 2-0 Kinsley Boys | Northern Counties East League Division One |
| 12 | Sat 3 Oct | 122-1 v Selby TownSelby Town 1-2 Winterton Rangers | Northern Counties East League Division One |
| 13 | Sat 10 Oct | 142-3 v Route One RoversWinterton Rangers 2-3 Route One Rovers | Northern Counties East League Division One |
| 14 | Wed 14 Oct | 71-5 v Appleby FrodinghamWinterton Rangers 1-5 Appleby Frodingham | Lincolnshire Senior Trophy First Round |
| 15 | Sat 17 Oct | 125-0 v Athersley RecreationAthersley Recreation 0-5 Winterton Rangers | Northern Counties East League Division One |
| 16 | Sat 24 Oct | 122-3 v Crowle ColtsWinterton Rangers 2-3 Crowle Colts | Northern Counties East League Division One |
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